New multi-component reactions
New multi-component reactions
The purpose of this thesis was to develop new high-throughput methodologies for the discovery and optimisation of multi-component reactions (MCRs) involving isocyanides. Initially, a novel method to synthesise isocyanides from the corresponding amines was developed using first a resin-supported benzotriazole and secondly a resin-supported sulfonyl chloride. This proved to be a highly efficient and clean technique to access this important class of compounds.
A tagging concept was then intensively studied focusing on the Ugi reaction, and validated to explore new directions. This involved, in particular, the use of a resin capture process, allowing only the compounds formed on the solid-support to be released after cleavage, and their tags analysed to identify the starting materials that were incorporated into the isolated product.
A methodology involving mass spectrometry was also examined to obtain rapid one-pot monomers reactivity profiles. This proved particularly useful in determination of the most efficient substrates and to allow exploration of the scope of the multi-component reactions.
Finally, a tagging concept developed around Ugi reactions was extended to a screening for new reactions and the results obtained following this strategy were reported, in particular a new reaction was found between an amine, an isocyanide and a carboxylic acid.
University of Southampton
Launay, Delphine
94085536-b1cf-4e4b-9042-9f019995bcce
2004
Launay, Delphine
94085536-b1cf-4e4b-9042-9f019995bcce
Launay, Delphine
(2004)
New multi-component reactions.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The purpose of this thesis was to develop new high-throughput methodologies for the discovery and optimisation of multi-component reactions (MCRs) involving isocyanides. Initially, a novel method to synthesise isocyanides from the corresponding amines was developed using first a resin-supported benzotriazole and secondly a resin-supported sulfonyl chloride. This proved to be a highly efficient and clean technique to access this important class of compounds.
A tagging concept was then intensively studied focusing on the Ugi reaction, and validated to explore new directions. This involved, in particular, the use of a resin capture process, allowing only the compounds formed on the solid-support to be released after cleavage, and their tags analysed to identify the starting materials that were incorporated into the isolated product.
A methodology involving mass spectrometry was also examined to obtain rapid one-pot monomers reactivity profiles. This proved particularly useful in determination of the most efficient substrates and to allow exploration of the scope of the multi-component reactions.
Finally, a tagging concept developed around Ugi reactions was extended to a screening for new reactions and the results obtained following this strategy were reported, in particular a new reaction was found between an amine, an isocyanide and a carboxylic acid.
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Published date: 2004
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Local EPrints ID: 465349
URI: http://eprints.soton.ac.uk/id/eprint/465349
PURE UUID: 72c97068-b88c-4683-b4f1-d2c7323e0c4a
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Date deposited: 05 Jul 2022 00:39
Last modified: 16 Mar 2024 20:07
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Author:
Delphine Launay
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